Dyes and process of making same.



UNITED STATES PATENT OFFICE.

HEINRICH HEIMANN, OF DESSAU, GERMANY; ASSIGNOR"TO ACTIEN GESELLSCHAF'I'F t-l3 ANILIN FABRIKATION, OF BERLIN, GERMANY.

DYES AND PROCESS OF MAKING SAME.

No Drawing.

To all whom it m ay concern:

Be it known that I, HEINRICH a citizen of the German Empire, residing atDessau, German my postoflice address being Friedrichchneider strasse015, Des sau,Germany, have Invented certain new and useful Improvementsin Dyesand Proc- I i and valuable sulfurized dyes. In order to obtain.such new dyes ari a-zo compound of the class above defined may be heatedwith sulfur to. higher temperatures; thus for instance para nitrobenzeneazo-ethyl alphanaphthylamin whenheated with sulfur to highertemperaturesyields a dyestufl which is distinguished by a=beautifulyellow brown tint and a good fastness. Furthermore a -mixtureofsucli anazo compound 'with an aromatic amin or with a, compound yielding such anaromatic amin, and more especially a mixture of such an a'zo compoundwith an azo compound of the aromatic series, or a mixture with anitroamin may be brought into reaction with sulfur thus yieldmg alsoethyl-alpha-naphthylamin and 20 parts of very valuable dyes of abeautiful tint'and of a good fastness.

' The. following examples serve to illus-- trate my invention, t weight:J i p (1.) 10 parts of para-mtrobenzene-azoe parts being by sulfur areheated during about 2-0 hours to say 180250 O. The melt thus obtainedis'treatedxwith a concentrated aqueous solution of sodium sulfid in orderto make the dye soluble; this may be separated as usual and roduces onunmordanted cotton a benlltlflll yellow brown, possessing a goodfastness a ainst boiling soap solution and boiling di uted acids. Thedye thus obtained is very similar to the roduct obtainable according toexample 4 rom a mixture oi are-nitrobenzene-azo-ethyl-alpha-naphthy aminwith meta toluylenediamin'. In a similar'mann'er new and valuable dyescan be obtained from para-'aminobenzene zoethyl-alplia-naphthylamin orfrom p raammobenzene-azo-ethyl-beta-naphthylamin from the former ,thereis obtained a yellow Specification of Iietters Eetent.

HEIMANN,

brown, whereas the latter yields a brown yellow.

(2.) 30 parts of benzene-azo-ethyl-alphanaphthylamin and 20 parts ofbenzidin are Patented Sept. 26. 1916. Application filed January 21,1915. Serial No. 3,607.

heated together with 100 parts of sulfur; a

the temperature may be kept. during about further about 1-3 hours to say260 to 280 4-6 hours at say ISO-250 C. and then for C. The .dye may berendered soluble as above; it dyes unmordanted cotton a beautiful deepyellow brown which is fast agalnstboiling soap and boiling diluted acidsand which possesses also a-ve'ry remarkable fastness against the actionof a' -d1luted hypochlorite solution.

-(3.)' A mixture of30 partsof' benzene-azohours to say 180250 'C. Thedyestufi after having been made soluble as indicatedethyl-alpha'naphthylamin, .25 parts of above )roduces on unmordantedcotton from j a dyeath containing an alkali metal sulfid beautiful anddeep brown-yellow tints of a j good fastncss to washing andto boilingdiluted acids. As to itsbehavior against theaction ofdilutedhypochlorite solutions it may be stated that it differs essentially fromthat of the ordinary sulfurized dyes. (4.) 10 parts ofmeta-toluylenediamin, 30- parts of para-nitrobenzene-azo-ethyl-alphaheated during about 2-4 hours to say 220- solvents; in concentratedsulfuric acid and n fuming sulfuric acid of 25 per cent.

SO it dissolves to a brown solution. The dye is easily soluble in analkali metal sulfid and in.

an alkaline hydrosulfite solution to'i'a yel-- low-brown solution.

nabhthylamin and 60-80 parts of sulfur are 200 C. The melt thus obtainedis treated It is obvious that the present invention is not limited tothe foregoing examples or to the details given therein. Thus it may be 7nieces? stated that the shades of the dyes ohtainable according to myinvention depend also, generally speaking, upon the proportions of theingredients as Well as upon other special conditions of reaction, suchas for instance the temperature of reaction and the duration of heating;furthermore the shades and the fastness of the new dyes obtainableaccording to my invention may be varied by such an alteration of theconditions of reaction,

-Whereas on the other hand in some cases it makes butlittle differenceas to shade and fastness or" the dyes Whether the respective azocompound 10f an l l-ethylarylamiu is treated with sulfur alone or inmixtures w th an aromatic amin or with a compound yielding such an amin.

Having now described niy invention what I claim is,--- v 1-. Newsulfurized dyes, which can be oh tained by the action of sulfur upon anace compound of an ll-ethy-larylemin obtainable by the'action ofaromatic compound upon an N-cthylarylarnin, which new dyes in the drystate and pulverized are dark poW-' ders, yielding, generally speaking,brown shades on unmordanted cotton to Washing and to boiling dilutedacids.

2. New sulfurized dyes, which can. be ob-' tained by the action ofsulfur upon 2:. nitroaz'o compound of an N-ethylarylamin, ob-

tai'nable by, the action of an aromatic nitrodmz'ov compound upon' an I!-etl1ylarylamin,

which" new dyes in the dry'state and pulver- 1 '35.

izedjarerdark powders, yielding, generally speak ng, brown shades onunmordanted cotton fast to Washing and to boiling diluted.

acids.

Newsulfurized dyes, which'can be ob tainedby theaction of sulfur upon anitro benzene-azo-N-ethylarylamin, obtainable. loy

the action of a nitrodiazobenzene-compound upon an l-l-ethylarylamin,which new dyes in the dry state and pulverized are dark powders,yielding, generally speaking, brown shades on unmordanted cotton fast towashit ingand to boiling diluted acids.

4. New sulfurized dyes, which can be obtained by the action of sulfurupon a; para:

insoluble or nearly insoluble in the. usual organic solvents and'whichdissolves in concentrated sulfuric acid and in fuming sulfurie acid ofSO tofu redflirown solu tion, which is not altered on thea ddition ofaluminium powder, and which newdye' is easily soluble in alkali metalsultid end in an alkaline h rlrosulfite solution to a ellow brownsclutiornthis new dye' d i on unmordanted cotton beautiful yellow crowntints fast to washing and to diluted boiling acids; I

6. The hereinhefore-described manufacture of new, dyes by acting withsulfur upon en ezc compound of an N-ethylarylamin, ob-

tainable by the action of an aromatic diuzo' compound uponN-ethylarylamm.

'2". The hereinbefore-described manufao ture of new dyes by acting withsulfur upon a nitro-azo compound of an N-ethylarylamin, obtainable bythev action of "a nitrodiazo compound upon an N-ethylarylamin.

8.. The hereinbefore-described manufacture cfnewdyes by acting withsulfur upon a Iiitrohenzeneazo-N-ethylnaphthylamin.

8, The hereinbefore-described manufacture of new dyes by acting withsulfur upon a para-nitrohenzeneazo N ethylnaphthyl- 21min.

in testimony whereof lhave hereunto set I my. hand in presenceof' twosubscribing Witnesses. I

' HEINRICH lPlElfli/IANN.

/Vitnesses:

ARTHUR REILLY, L. @GHLMANN.

